Methanol → HCID 67545283, compound

HRID 2176170Notes

Reaction equation

HRID 2176170 reaction equation
C[Si]([CH:5]=[N+:6]=[N-])(C)C.N12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([C:11]3=[O:18])[CH2:9]1)[CH2:15]2.CO.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(O)(=O)C>[N:6]12[CH2:5][CH:10]3[CH2:16][CH:14]([CH2:13][CH:12]([C:11](=[O:18])[CH2:9]3)[CH2:17]1)[CH2:15]2

Participants

7

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-oneHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 67545283HCID 67545283, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of trimethylsilyldiazomethane (2 N in hexanes, 9.00 mL, 18.00 mmol; Aldrich) was added a solution of 1-azaadamantan-4-one (2.268 g, 15 mmol; Becker, D. P.; Flynn, D. L. Synthesis 1992, 1080) in tetrahydrofuran (12 mL) dropwise over 20 minutes Anhydrous methanol (6 mL) was added and the mixture was allowed to warm to room temperature. After 18 hours, glacial acetic acid was added dropwise until the mixture was colorless (about 1 mL). The reaction mixture was shaken with saturated sodium carbonate (4 mL), the tetrahydrofuran layer was separated, and the aqueous portion was extracted with dichloromethane (3×12 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to give the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 1.72 (m, 1H), 1.78 (dddd, J=13.6, 4.0, 2.4, 2.1 Hz, 1H), 1.88 (m, 1H), 1.90 (dddd, J=14.6, 4.0, 2.4, 2.1 Hz, 1H), 2.14 (dddd, J=14.4, 6.5, 4.4, 1.9 Hz, 1H), 2.27 (m, 1H), 2.59 (t, J=5.8 Hz, 1H), 2.63-2.68 (m, 2H), 2.96 (m, 1H), 3.01 (dd, J=4.4, 2.0 Hz, 1H), 3.07 (m, 1H), 3.14 (m, 1H), 3.25 (ddd, J=14.6, 4.9, 1.2 Hz, 1H), 3.43 (dd, J=14.2, 5.1 Hz, 1H); MS (DCI/NH3) m/z 166 (M+H)+.

Workup

  1. additionwas added
  2. customthe tetrahydrofuran layer was separated
  3. extractionthe aqueous portion was extracted with dichloromethane (3×12 mL)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d40414e0a88c40919e177071de16f750
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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